How to Balance Experience and Youth for Powerful Leadership

Chip Conley is an entrepreneur, bestselling author, and self-proclaimed “modern elder.” After nearly 25 years of founding and running one of the world’s most successful boutique hotel chains, Joie de Vivre Hospitality, Conley joined Airbnb as the head of global hospitality and strategy, just as the company transitioned from promising startup to disruptive global market-maker.

Conley’s new book, Wisdom at Work, reflects on the new realities of a five-generation workforce and how the wisdom of age and experience can benefit the speed of digitization and technology. Conley shared his experience as Airbnb founder Brian Chesky’s “mentern” and how that shaped his values of diversity and inclusion.

Lisa Kay Solomon:Wisdom at Work explores the role of “modern elders” in this increasingly digital world. What is a modern elder and why do you believe they are so important to organizations focused on speed and growth?

Chip Conley: The term “modern elder” is one I developed to describe a new reality in our society—one where older workers pair their skills and experiences with those of less seasoned executives. This can happen in the context of fast-growing companies reinventing our economy as well as from non-profits and legacy companies. A modern elder has liberated the word “elder” from the historically derogatory term “elder-ly” and is a highly valued asset in ways concrete and abstract.

Anyone with meaningful experience—generally a decade or more older than those that surround them—can reinvent themselves as a modern elder by becoming unafraid of change, insatiable in intellectual curiosity, interested in big things, and happy in small ways. Whether in their 40s, 50s, 60s, or beyond, modern elders are both student and sage, mentor and intern, and have a thirst for mastery.

In this historic time, when there are five generations simultaneously in the workforce, the modern elder can play a critical role up and down the organizational chart, from quietly mentoring senior, but less seasoned leaders, to serving as a source of ideas that impact an entire organization’s culture based on previous experience and best practices.

LKS: You joined Airbnb back in 2013 as a somewhat “reluctant disruptor” after selling your very successful hotel company, Joie de Vivre, and you became a “mentern” (mentor + intern) to CEO Brian Chesky. What inspired you to take the leap?

CC: Brian silently asked me a provocative question when I first met him: “How would you like to democratize the hospitality business?” Having spent my entire career in the hospitality industry building the country’s second-largest boutique hotel company, I was both intrigued and taken aback by the audacity of Brian’s question and his description of his vision for Airbnb.

I had sold Joie de Vivre Hospitality a few years earlier, and a few tech-minded friends told me Airbnb was a rocket ship ready to launch. My gut told me that home sharing might just be scaling the experientially-minded “live like a local” ethos that boutique hotels had pioneered for the previous quarter-century.

So, I decided to take the leap—a leap I initially thought would be a 15 hour per week advisory role but turned into a 15 hour per day full-time job. And it also turned into one of the great chapters of my life.

LKS: In your book you talk about the importance of finding new ways to blend EQ (emotional intelligence) and DQ (digital intelligence). What’s required to create an environment where both are honored and supported?

CC: There’s an implicit trade agreement between boomers (and GenXers) and millennials: emotional intelligence (EQ) for digital intelligence (DQ). The rare individual may possess both, but in most high-growth technology companies, the modern elder possesses the lion’s share of EQ gained during life and career experiences, while the younger, tech-savvy leaders possess far more technical skills and DQ.

The culture necessary to honor, support, and share both EQ and DQ has to do with individual and organizational DNA. The modern elder generally is able to create trust through his or her deep knowledge and connection of an industry that younger cohorts are looking to disrupt. But the successful modern elder also mixes his or her superior number of life experiences with a strong dose of humility and relevancy, as his or her younger colleagues aren’t looking for a history lesson.

LKS: There’s a lot of discussion about diversity and inclusion these days, with a particular focus on equality for gender and ethnicity. You focus on the importance of age diversity. Why is that so important?

CC: When we used to speak of age diversity, it was often around the men and women nearing the traditional retirement age in their 60s. Today, it’s a whole new world. We have executives with median ages in their 20s running some of the largest and most influential companies in the world. Facebook, Google, and Apple have median employee ages of 28, 30, and 31. No matter their digital intelligence, it seems realistic to ask if these executives have the seasoning to be building and managing multi-billion-dollar businesses without the benefit of some more seasoned colleagues.

Enter the modern elder.

The modern elder can help balance the vision, passion, energy, and drive of these young masters of the universe with the real-world experience gained through a decade or more of work.

Age diversity is often the difference between a great idea and a great company. Would Facebook be what it is today if not for Sheryl Sandberg’s role as the modern elder to Zuckerberg? The examples of others with brilliant founders who have either succeeded wildly or flamed out spectacularly are countless based to some degree on whether or not a visionary leader was paired with a modern elder.

LKS: What is your advice to ambitious entrepreneurs on how they can engage and benefit from “modern elders”?

CC: Brian has a huge appetite for learning. He has a growth mindset, so beyond just reaching out to me, he’s never been shy to connect with a thought leader to learn from them. Another way to engage a wise counselor is to suggest a mutual mentorship, in which both of you can teach each other something of value, much like the EQ for DQ relationship I mentioned earlier. A modern elder is naturally curious, so you may have something to teach them, and the modern elder will likely possess some or all of the five attributes from which the ambitious entrepreneur can benefit:

Good judgment: Modern elders have a long-term perspective based on the wisdom they’ve gathered over the years.

Unvarnished insight: A modern elder can cut through the clutter quickly to find the core issue that needs attention, whether in a job interview or a strategic discussion.

Emotional intelligence: Modern elders are self-aware, patient, and empathetic people who are good at both understanding and managing their own emotions, and tuning in to the emotions of others.

Holistic thinking: The modern elder’s brain has the capacity to traverse from one side to the other more adeptly, dispassionately recognizing patterns more easily.

Stewardship: The modern elder wants to put his or her lifetime of experience and perspective to work to positively impact future generations and has moved from success to significance in their life.

Lisa Kay Solomon is a well-known thought leader in design innovation with a focus on helping leaders learn how to be more creative, flexible and resilient in the face of constant change. Lisa is the Chair of Transformational Practices and Leadership at Singularity University a global community of smart, passionate, action-oriented leaders who want to use exponential technologies to positively...